JPS6334176B2 - - Google Patents
Info
- Publication number
- JPS6334176B2 JPS6334176B2 JP61121416A JP12141686A JPS6334176B2 JP S6334176 B2 JPS6334176 B2 JP S6334176B2 JP 61121416 A JP61121416 A JP 61121416A JP 12141686 A JP12141686 A JP 12141686A JP S6334176 B2 JPS6334176 B2 JP S6334176B2
- Authority
- JP
- Japan
- Prior art keywords
- quaternary ammonium
- bisphenol
- solvent
- mixture
- epihalohydrin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 20
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 15
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 15
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical group CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 15
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000003822 epoxy resin Substances 0.000 claims description 12
- 229920000647 polyepoxide Polymers 0.000 claims description 12
- 229930185605 Bisphenol Natural products 0.000 claims description 11
- -1 quaternary ammonium halide Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 8
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 6
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 150000003944 halohydrins Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 125000001183 hydrocarbyl group Chemical group 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical group [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000003518 caustics Substances 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000007033 dehydrochlorination reaction Methods 0.000 description 7
- 235000013824 polyphenols Nutrition 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical class CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- GCHQFFZKSQTAMA-UHFFFAOYSA-N propane-1,2,3-triol;dihydrochloride Chemical compound Cl.Cl.OCC(O)CO GCHQFFZKSQTAMA-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000008096 xylene Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/737,955 US4582892A (en) | 1985-05-28 | 1985-05-28 | Process for the preparation of epoxy resins |
| US737955 | 1985-05-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61278525A JPS61278525A (ja) | 1986-12-09 |
| JPS6334176B2 true JPS6334176B2 (fr) | 1988-07-08 |
Family
ID=24965965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61121416A Granted JPS61278525A (ja) | 1985-05-28 | 1986-05-28 | エポキシ樹脂の製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4582892A (fr) |
| EP (1) | EP0203473B1 (fr) |
| JP (1) | JPS61278525A (fr) |
| KR (1) | KR900001942B1 (fr) |
| AU (1) | AU593801B2 (fr) |
| BR (1) | BR8602404A (fr) |
| CA (1) | CA1236633A (fr) |
| DE (1) | DE3684360D1 (fr) |
| ES (1) | ES8706748A1 (fr) |
| NZ (1) | NZ216266A (fr) |
| PH (1) | PH22604A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0278565U (fr) * | 1988-12-01 | 1990-06-15 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2059307T3 (es) * | 1985-12-13 | 1994-11-16 | Ciba Geigy Ag | Procedimiento para la preparacion de compuestos glicidilo. |
| US4672103A (en) * | 1986-02-14 | 1987-06-09 | The Dow Chemical Company | Non-sintering epoxy resins prepared from triglycidyl ethers and epihalohydrins |
| US4663400A (en) * | 1986-04-28 | 1987-05-05 | The Dow Chemical Company | Epoxy resins prepared from trisphenols and dicyclopentadiene |
| EP0406438B1 (fr) * | 1988-12-26 | 1994-03-16 | Kowa Company Ltd. | Production d'ether de glycidyle |
| GB9204600D0 (en) * | 1992-03-03 | 1992-04-15 | Dow Deutschland Inc | Method of reducing the concentration of a liquid resin in an aqueous composition |
| US5844062A (en) * | 1997-04-29 | 1998-12-01 | Industrial Technology Research Institute | Process for preparing phenolepoxy resins in the absence of an aqueous phase |
| CN104710597A (zh) | 2008-03-25 | 2015-06-17 | 陶氏环球技术有限责任公司 | 制备液体环氧树脂的方法 |
| CN101613458B (zh) * | 2008-06-25 | 2013-06-05 | 中国石油化工集团公司 | 一种双酚a型液体环氧树脂的制备方法 |
| TW201035150A (en) | 2009-02-26 | 2010-10-01 | Dow Global Technologies Inc | Epoxy resin production |
| US9469720B2 (en) | 2011-12-19 | 2016-10-18 | Blue Cube Ip Llc | Epdxy resin production |
| JP5956159B2 (ja) * | 2012-01-13 | 2016-07-27 | 株式会社Adeka | グリシジルエーテルの製造方法 |
| JP2019104883A (ja) * | 2017-12-14 | 2019-06-27 | 旭化成株式会社 | エポキシ樹脂、エポキシ樹脂組成物、硬化物、及びエポキシ樹脂の製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5413596A (en) * | 1977-06-30 | 1979-02-01 | Shell Int Research | Preparation of polyglycidyl ether of polyphenol |
| JPS5687576A (en) * | 1979-11-24 | 1981-07-16 | Hoechst Ag | Manufacture of glycidyl etger of monohydric or polyhydric phenol*glycidyl ether thereof and its use |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL98450C (fr) * | 1955-03-28 | |||
| US2943096A (en) * | 1957-05-10 | 1960-06-28 | Union Carbide Corp | Preparation of monomeric glycidyl polyethers of polyhydric phenols |
| US3221032A (en) * | 1960-04-18 | 1965-11-30 | Devoe & Raynolds Co | Continuous process for the preparation of glycidyl polyethers |
| NL270270A (fr) * | 1960-10-17 | |||
| US3372142A (en) * | 1964-01-31 | 1968-03-05 | Dow Chemical Co | Epoxidation process |
| IT1012923B (it) * | 1974-05-30 | 1977-03-10 | Sir Soc Italiana Resine Spa | Procedimento per la preparazione continua di eteri poliglicidilici di fenoli poliossidrilici |
| GB2001991B (en) * | 1977-06-30 | 1982-01-06 | Shell Int Research | Preparation of polyglycidyl ethers of polyhydric phenols |
| FR2450266A1 (fr) * | 1979-03-02 | 1980-09-26 | Rhone Poulenc Ind | Procede de preparation de polyesthers glycidiques de polyphenols |
| US4313886A (en) * | 1980-09-25 | 1982-02-02 | The Dow Chemical Company | Process for preparing liquid epoxy resins |
| US4390680A (en) * | 1982-03-29 | 1983-06-28 | The Dow Chemical Company | Phenolic hydroxyl-containing compositions and epoxy resins prepared therefrom |
| US4499255B1 (en) * | 1982-09-13 | 2000-01-11 | Dow Chemical Co | Preparation of epoxy resins |
-
1985
- 1985-05-28 US US06/737,955 patent/US4582892A/en not_active Expired - Fee Related
-
1986
- 1986-05-14 CA CA000509183A patent/CA1236633A/fr not_active Expired
- 1986-05-15 AU AU57472/86A patent/AU593801B2/en not_active Ceased
- 1986-05-15 EP EP86106656A patent/EP0203473B1/fr not_active Expired - Lifetime
- 1986-05-15 DE DE8686106656T patent/DE3684360D1/de not_active Expired - Fee Related
- 1986-05-22 NZ NZ216266A patent/NZ216266A/en unknown
- 1986-05-26 PH PH33815A patent/PH22604A/en unknown
- 1986-05-27 ES ES555350A patent/ES8706748A1/es not_active Expired
- 1986-05-27 BR BR8602404A patent/BR8602404A/pt unknown
- 1986-05-28 JP JP61121416A patent/JPS61278525A/ja active Granted
- 1986-05-28 KR KR1019860004186A patent/KR900001942B1/ko not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5413596A (en) * | 1977-06-30 | 1979-02-01 | Shell Int Research | Preparation of polyglycidyl ether of polyphenol |
| JPS5687576A (en) * | 1979-11-24 | 1981-07-16 | Hoechst Ag | Manufacture of glycidyl etger of monohydric or polyhydric phenol*glycidyl ether thereof and its use |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0278565U (fr) * | 1988-12-01 | 1990-06-15 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES555350A0 (es) | 1987-07-01 |
| EP0203473A3 (en) | 1988-06-15 |
| KR860009057A (ko) | 1986-12-19 |
| US4582892A (en) | 1986-04-15 |
| EP0203473A2 (fr) | 1986-12-03 |
| DE3684360D1 (de) | 1992-04-23 |
| PH22604A (en) | 1988-10-17 |
| AU593801B2 (en) | 1990-02-22 |
| ES8706748A1 (es) | 1987-07-01 |
| JPS61278525A (ja) | 1986-12-09 |
| EP0203473B1 (fr) | 1992-03-18 |
| NZ216266A (en) | 1988-05-30 |
| AU5747286A (en) | 1986-12-04 |
| BR8602404A (pt) | 1987-01-21 |
| CA1236633A (fr) | 1988-05-10 |
| KR900001942B1 (ko) | 1990-03-26 |
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